Urea, (2,3-dihydro-2-oxo-3-(1-(1H-pyrrol-2-yl)ethylidene)-1H-indol-5-yl)-

Base Information

• Chemical Name: Urea, (2,3-dihydro-2-oxo-3-(1-(1H-pyrrol-2-yl)ethylidene)-1H-indol-5-yl)-
• CAS No.: 850717-64-5
• Molecular Formula: C₁₅H₁₄N₄O₂
• Molecular Weight: 282.302
• UNII: SYV8VN8W5K
• Nikkaji Number: J3.422.708J
• Wikidata: Q27289467
• Pharos Ligand ID: QDZ7U5RZPFCC
• ChEMBL ID: CHEMBL228654
• Mol file: 850717-64-5.mol

Synonyms:BX 517;BX-517;BX517 cpd

Chemical Property of Urea, (2,3-dihydro-2-oxo-3-(1-(1H-pyrrol-2-yl)ethylidene)-1H-indol-5-yl)-

Chemical Property:

• PSA: 100.01000
• LogP: 3.29940
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥8.55 mg/mL in DMSO
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 282.11167570
• Heavy Atom Count: 21
• Complexity: 488

Purity/Quality:

99%, ^*data from raw suppliers

BX-517 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C1C2=C(C=CC(=C2)NC(=O)N)NC1=O)C3=CC=CN3
• Isomeric SMILES: C/C(=C/1\C2=C(C=CC(=C2)NC(=O)N)NC1=O)/C3=CC=CN3
• Uses: BX-517 is a potent and selective inhibitor of PDK1 that binds to the ATP binding pocket of the protein (IC50 = 6 nM).

Technology Process of Urea, (2,3-dihydro-2-oxo-3-(1-(1H-pyrrol-2-yl)ethylidene)-1H-indol-5-yl)-

There total 5 articles about Urea, (2,3-dihydro-2-oxo-3-(1-(1H-pyrrol-2-yl)ethylidene)-1H-indol-5-yl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

C14H13N3O (946843-76-1) + trimethylsilyl isocyanate (1118-02-1) → BX-517 (850717-64-5,946843-63-6)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/j.bmcl.2007.04.071

Reference yield:

C14H11N3O3 (946843-72-7) → BX-517 (850717-64-5,946843-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / H₂ / Pd/C / methanol / 2068.65 Torr

2: 89 percent / tetrahydrofuran

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2007.04.071

Reference yield:

5-nitrooxindole (20870-79-5) → BX-517 (850717-64-5,946843-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine / 130 °C

2: 85 percent / H₂ / Pd/C / methanol / 2068.65 Torr

3: 89 percent / tetrahydrofuran

With piperidine; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2007.04.071

upstream raw materials:

C₁₄H₁₃N₃O

trimethylsilyl isocyanate

C₁₄H₁₁N₃O₃

5-nitrooxindole